Methyl isothiocyanate → HCID 14183054, compound

HRID 1722161Notes

Reaction equation

HRID 1722161 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:23][N:24]=[C:25]=[S:26]>C1(C)C=CC=CC=1>[CH3:23][NH:24][C:25]([N:20]1[CH2:21][CH2:22][CH:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[N:9]=2)[CH2:18][CH2:19]1)=[S:26]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 22397358HCID 22397358, compound

Product 1

HCID 14183054HCID 14183054, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 4-[1-(4-fluorophenyl)-1H-indazol-3-yl]piperidine-1-carbonitrile of Example 102 (30 g, 0.094 moles) and 25% H2SO4 (225 ml) was refluxed for 20 hours. The mixture was cooled, poured into H2O, and basified with a 25% NaOH solution. The product was extracted (dichloromethane), dried (MgSO4), and concentrated to yield 21 g (76%) of 1-(4-fluorophenyl)-3-(4-piperidinyl)-1H-indazole as an oil. To a stirred suspension of the indazole (4.0 g, 0.0135 moles) in toluene (70 ml) was added dropwise methyl isothiocyanate (1.5 ml, 0.022 moles). The mixture was stirred for 23 hours at ambient temperature during which time the product precipitated from the solution. The product was collected and recrystallized twice from isopropyl alcohol to yield 2.74 g (55%) of N-methyl-4-[1-(4-fluorophenyl)-1H-indazol-3-yl]piperidine-1-carbothioamide, m.p. 179°-181° C.

Workup

  1. customprecipitated from the solution
  2. customThe product was collected
  3. customrecrystallized twice from isopropyl alcohol

Sources & evidence

ORD record
ord-516cb13733694b438b8e829b71621edb
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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